In this paper, I sketch the CP layer in the main and embedded clause in the history of English. The Modern English main clause is not as easily expandable as the Old English one but the reverse is true in the subordinate clause where Modern English has a more flexible embedded CP than Old English. I’ll focus on the developments of the embedded CP. It has been claimed that Old English lacks an embedded split CP and therefore lacks embedded V2 and a host of other embedded root phenomena. I show this to be true for complements to both assertive and non-assertive verbs. In contrast, the Modern English matrix verb has an effect on the strength of the C-position. Assertive verbs in Modern English allow main clause phenomena in subordinate clauses whereas non-assertives typically don’t. The main point of the paper will be to chronicle the changes that `stretch’ the embedded clause and the changing role of main verbs. It is descriptive rather than explanatory, e.g. in terms of changes in phase-head status.